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PubMed2005

Echinacea alkamide disposition and pharmacokinetics in humans after tablet ingestion.

Echinacea is a widely used herbal remedy for the treatment of colds and other infections. However, almost nothing is known about the disposition and pharmacokinetics of any of its components, particularly the alkamides and caffeic acid conjugates which are thought to be the active phytochemicals. In this investigation, we have examined serial plasma samples from 9 healthy volunteers who ingested echinacea tablets manufactured from ethanolic liquid extracts of Echinacea angustifolia and Echinacea purpurea immediately after a standard high fat breakfast. Caffeic acid conjugates could not be identified in any plasma sample at any time after tablet ingestion. Alkamides were rapidly absorbed and were measurable in plasma 20 min after tablet ingestion and remained detectable for up to 12 h. Concentration-time curves for 2,4-diene and 2-ene alkamides were determined. The maximal concentrations for the sum of alkamides in human plasma were reached within 2.3 h post ingestion and averaged 336+/-131 ng eq/mL plasma. No obvious differences were observed in the pharmacokinetics of individual or total alkamides in 2 additional fasted subjects who took the same dose of the echinacea preparation. This single dose study provides evidence that alkamides are orally available and that their pharmacokinetics are in agreement with the one dose three times daily regimen already recommended for echinacea.

Adult↗
PubMedDate not supplied

Plant phenolics protect from bleomycin-induced oxidative stress and mutagenicity in Salmonella typhimurium TA102.

Antioxidants are deemed to be important against DNA damage and mutations induced by reactive oxygen species (ROS). An assay for the ability of plant phenolics to protect against mutations caused by bleomycin treatment in Salmonella typhimurium TA102 cells in concentrations up to 20 microM was developed. Caffeic acid, gallic acid, protocatechuic acid, ferulic acid and rutin hydrate in final concentrations of 0.5 to 20 microM were tested for their ability to protect TA102 cells from mutations caused by oxidative stress from bleomycin. The cut-off concentration of 20 microM was used because as a limit it is biologically meaningful, higher concentrations being unrealistic in vivo. Caffeic acid was very potent at a concentration of 0.5-20 microM. The other four antioxidants were not effective up to 20 microM. The above assay will be helpful to characterize antioxidant molecules.

Antimetabolites, Antineoplastic↗
PubMed2005

Rosmarinic acid, a new snake venom phospholipase A2 inhibitor from Cordia verbenacea (Boraginaceae): antiserum action potentiation and molecular interaction.

Many plants are used in traditional medicine as active agents against various effects induced by snakebite. The methanolic extract from Cordia verbenacea (Cv) significantly inhibited paw edema induced by Bothrops jararacussu snake venom and by its main basic phospholipase A2 homologs, namely bothropstoxins I and II (BthTXs). The active component was isolated by chromatography on Sephadex LH-20 and by RP-HPLC on a C18 column and identified as rosmarinic acid (Cv-RA). Rosmarinic acid is an ester of caffeic acid and 3,4-dihydroxyphenyllactic acid [2-O-cafeoil-3-(3,4-di-hydroxy-phenyl)-R-lactic acid]. This is the first report of RA in the species C. verbenacea ('baleeira', 'whaler') and of its anti-inflammatory and antimyotoxic properties against snake venoms and isolated toxins. RA inhibited the edema and myotoxic activity induced by the basic PLA2s BthTX-I and BthTX-II. It was, however, less efficient to inhibit the PLA2 activity of BthTX-II and, still less, the PLA2 and edema-inducing activities of the acidic isoform BthA-I-PLA2 from the same venom, showing therefore a higher inhibitory activity upon basic PLA2s. RA also inhibited most of the myotoxic and partially the edema-inducing effects of both basic PLA2s, thus reinforcing the idea of dissociation between the catalytic and pharmacological domains. The pure compound potentiated the ability of the commercial equine polyvalent antivenom in neutralizing lethal and myotoxic effects of the crude venom and of isolated PLA2s in experimental models. CD data presented here suggest that, after binding, no significant conformation changes occur either in the Cv-RA or in the target PLA2. A possible model for the interaction of rosmarinic acid with Lys49-PLA2 BthTX-I is proposed.

Animals↗
PubMed1982

Inhibition of the mutagenicity of bay-region diol epoxides of polycyclic aromatic hydrocarbons by naturally occurring plant phenols: exceptional activity of ellagic acid.

Ferulic, caffeic, chlorogenic, and ellagic acids, four naturally occurring plant phenols, inhibit the mutagenicity and cytotoxicity of (+/-)-7beta,8alpha-dihydroxy-9alpha, 10alpha-epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene (B[a]P 7,8-diol-9,10-epoxide-2), the only known ultimate carcinogenic metabolite of benzo[a]pyrene. The mutagenicity of 0.05 nmol of B[a]P 7,8-diol-9,10-epoxide-2 in strain TA100 of Salmonella typhimurium is inhibited 50% by incubation of the bacteria and the diol epoxide with 150 nmol of ferulic acid, 75 nmol of caffeic acid, 50 nmol of chlorogenic acid or, most strikingly, 1 nmol of ellagic acid in the 0.5-ml incubation mixture. A 3-nmol dose of ellagic acid inhibits mutation induction by 90%. Ellagic acid is also a potent antagonist of B[a]P 7,8-diol-9,10-epoxide-2 in Chinese hamster V79 cells. Mutations to 8-azaguanine resistance induced by 0.2 muM diol epoxide are reduced by 50% when tissue culture media also contains 2 muM ellagic acid. Similar to results obtained with the bacteria, ferulic, caffeic, and chlorogenic acids are approximately two orders of magnitude less active than ellagic acid in the mammalian cell assay. The antimutagenic effects of the plant phenols result from their direct interaction with B[a]P 7,8-diol-9,10-epoxide-2, because a concentration-dependent increase in the rate of diol epoxide disappearance in cell-free solutions of 1:9 dioxane/water, pH 7.0, is observed with all four phenols. In parallel with the mutagenicity studies, ellagic acid is 80-300 times more effective than the other phenols in accelerating the disappearance of B[a]P 7,8-diol-9,10-epoxide-2. Ellagic acid at 10 muM increases the disappearance of B[a]P 7,8-diol-9,10-epoxide-2 by approximately 20-fold relative to the spontaneous and hydronium ion-catalyzed hydrolysis of the diol epoxide at pH 7.0. Ellagic acid is a highly potent inhibitor of the mutagenic activity of bay-region diol epoxides of benzo[a]pyrene, dibenzo[a,h]pyrene, and dibenzo[a,i]pyrene, but higher concentrations of ellagic acid are needed to inhibit the mutagenic activity of the chemically less reactive bay-region diol epoxides of benz[a]anthracene, chrysene, and benzo[c]phenanthrene. These studies demonstrate that ellagic acid is a potent antagonist of the adverse biological effects of the ultimate carcinogenic metabolites of several polycyclic aromatic hydrocarbons and suggest that this naturally occurring plant phenol, normally ingested by humans, may inhibit the carcinogenicity of polycyclic aromatic hydrocarbons.

Animals↗
PubMed2006

Echinacea alkylamides inhibit interleukin-2 production by Jurkat T cells.

Alkylamides present in Echinacea species have reported immunomodulatory actions, yet their direct effects on T lymphocytes, key mediators of antiviral immunity, are poorly understood. We hypothesized that constituents present in ethanolic extracts of Echinacea species exert direct immunomodulatory effects on human Jurkat T cells. Modulation of IL-2 production by submaximally stimulated Jurkat cells was determined in response to treatment with extracts prepared from dried aerial parts of Echinacea purpurea. Cells were treated with the extracts, with alkylamides or caffeic acid derivatives isolated from Echinacea species, or with corresponding ethanol vehicle, in the absence or presence of phytohemagglutinin and phorbal ester. E. purpurea extracted in a solvent mixture of 95:5 ethanol/water dose-dependently inhibited IL-2 production. This IL-2 inhibitory activity correlated with the presence of alkylamides but not caffeic acid derivatives, as determined by high performance liquid chromatography/electrospray ionization-mass spectrometry analysis. Simultaneous measurement of secreted IL-2 by ELISA and cell viability by the XTT assay showed that the 95:5 ethanol/water extract of E. purpurea was both IL-2 suppressive and cytotoxic at 50 and 100 microg/mL. Lower concentrations from 6.25 to 25 microg/mL significantly decreased IL-2 production but not cell viability. Alkylamides at concentrations found in a 50 microg/mL extract decreased IL-2 production by approximately 50%. Two Echinacea-derived alkylamides significantly depressed IL-2 production but not cell viability in a dose-dependent manner. Thus, alkylamides present in E. purpurea suppress the ability of activated Jurkat T cells to produce IL-2 independently of direct, cytotoxic effects.

Amides↗
PubMed2005

DPPH radical-scavenging effect of several phenylpropanoid compounds and their glycoside derivatives.

Eugenol, isoeugenol, caffeic acid, ferulic acid, isoferulic acid, estragole, trans-anethole, and paeonol are components of a Chinese herbal medicine used as a painkiller and stomachic. We investigated the potential role of these compounds as antioxidants. We studied the DPPH (1,1-diphenyl-2-picrylhydrazyl) radical-scavenging effect of these molecules, together with some glycoside derivatives, to ascertain their potential in reducing the levels of activated oxygen species in vivo. The DPPH radical-scavenging effects of eugenol, isoeugenol, and the glycoside derivatives of caffeic acid, ferulic acid, and isoferulic acid (SC(50)=8-28 microM) were similar to those of alpha-tocopherol, which was used as a positive control.

Antioxidants↗
PubMedDate not supplied

Evaluation of sage phenolics for their antileishmanial activity and modulatory effects on interleukin-6, interferon and tumour necrosis factor-alpha-release in RAW 264.7 cells.

A series of sage phenolics was tested for activity against a panel of Leishmania parasites and for immunomodulatory effects on macrophage functions including release of tumour necrosis factor (TNF), interleukin-6 (IL-6), and interferon (IFN)-like activities. For this, functional bioassays were employed including an in vitro model for leishmaniasis in which macrophage-like RAW 264.7 cells were infected with Leishmania parasites, an extracellular Leishmania growth-inhibition assay, a fibroblast-lysis assay for TNF-activity, a cell proliferation assay using IL-6 sensitive murine B9 hybridoma cells, and a virus protection assay for IFN-like activity. Whereas none of the test samples exhibited marked activities against extracellular Leishmania promastigotes (IC50 > 700 to > 2800 nM; > 500 microg/ml), caffeic acid, salvianolic acids K and L as well as the methyl ester of salvianolic acid I showed pronounced antileishmanial activities against intracellular amastigote stages within RAW cells (IC50 3-23 nM vs. 10-11 nM for the reference Pentostam). Noteworthy, the phenolic samples showed no cytotoxicity against the host cells (IC50 > 600 to > 2200 nM; > 400 microg/ml). Tested sage phenolics activated Leishmania-infected RAW 264.7 for release of TNF ranging 22-117 U/ml and IL-6 ranging 3-42 U/ml. In contrast, their TNF- or IL-6-inducing potential in experiments with non-infected host cells was negligible. Furthermore, caffeic acid and salvianolic acid K induced a modest release of IFN-like activity (5-9 and 2-4 U/ml, respectively) as reflected by inhibition of the cytopathic effect of encephalomyocarditis virus on L929 cells. The results support the emerging picture that plant polyphenols may be credited for the profound health-beneficial properties of various herbal medicines and agricultural products.

Animals↗
PubMed2002

Plant-derived phenolic compounds prevent the DNA single-strand breakage and cytotoxicity induced by tert-butylhydroperoxide via an iron-chelating mechanism.

The protective effects of selected members from a series of caffeic acid esters and flavonoids were tested in various toxicity paradigms using U937 cells, previously shown to be sensitive to either iron chelators or bona fide radical scavengers or to both classes of compounds. It was found that all the protective polyphenols were active at very low concentrations and that their effects were observed only under those conditions in which iron chelators also afforded protection. Consistently, active polyphenolic compounds, unlike the inactive ones, effectively chelated iron in an in vitro system. It follows that, at least under the experimental conditions utilized in the present study, the most prominent activity of these polyphenolic compounds resides in their ability to chelate iron. Further studies revealed that the protective effects afforded by the caffeic acid esters and flavonoids were largely mediated by the catechol moiety and that the relative biological potency of these compounds was a direct function of their lipophilicity.

Caffeic Acids↗
PubMed1997

[Chemical constituents of Cuscuta austrolis R.Br].

Australiside A(1), a new diterpenoid glucoside, was isolated together with thymidine(2), caffeic acid(3), p-coumaric acid(4) and caffeic-beta-D-glucoside(5) from Cuscuta australis. Based on spectral analysis and physico-chemical properties the structures of the above-cited five compounds were identified. The structure of compound 1 was deduced as 4-oic acid-7-oxo-kaurene-6 alpha-O-beta-D-glucoside. Compounds 2, 3, 4 and 5 were obtained from Cuscuta for the first time.

Caffeic Acids↗
PubMed2004

Oral flavonoid supplementation attenuates atherosclerosis development in apolipoprotein E-deficient mice.

OBJECTIVE: Caffeic acid phenethyl ester (CAPE), a natural flavonoid, specifically blocks activation of nuclear factor-kappaB (NF-kappaB). We examined the effects of oral CAPE supplementation on atherogenesis in apolipoprotein E-deficient (apoE-/-) mice. METHODS AND RESULTS: Ten-week-old male apoE-/- mice were supplemented orally with CAPE (30 mg/kg body weight) for 12 weeks. At the end of administration, atherosclerosis progression, NF-kappaB activity, gene expression profiling by microarray analysis, and oxidative stress were studied. Treatment of apoE-/- mice with CAPE significantly reduced aortic atherosclerosis, NF-kappaB activity, and expression of NF-kappaB-related genes in the aorta. Moreover, expression of other gene clusters such as basic transcription factors, growth factors, cytokines, cell adhesion proteins, and extracellular matrix were also significantly reduced by treatment with CAPE. Plasma isoprostane level in apoE-/- mice was also significantly reduced by CAPE. CONCLUSIONS: In apoE-/- mice, oral CAPE supplementation attenuates the atherosclerotic process. This may be attributable to direct inhibition of NF-kappaB in the lesion and reduction of systemic oxidative stress. In apoE-/- mice, oral caffeic acid phenethyl ester (CAPE) supplementation attenuates the atherosclerotic process and reduces NF-kappaB activity and expression of NF-kappaB-related genes in the aorta. This may be attributable to direct inhibition of NF-kappaB in the lesion and reduction of systemic oxidative stress.

Animals↗
PubMed1997

Application of a new high-performance liquid chromatographic method for measuring selected polyphenols in human plasma.

We developed a method to measure plasma levels of selected polyphenols before and after ingestion of green tea. Blood samples were obtained from four healthy women before and 30 and 50 min after the ingestion of 300 ml of green tea infusion. A 1-ml volume of plasma was hydrolysed with 0.5 M HCl-methanol (1:1, v/v) for 30 min at room temperature, extracted with ethyl acetate and separated by reversed-phase chromatography. Polyphenols were identified on the basis of their retention times and by spectrum analysis. Green tea caffeine has the same retention times as caffeic acid. Consumption of green tea produces a notable increase in the plasma levels of caffeine plus caffeic acid and the appearance of measurable levels of epigallocatechingallate. In conclusion, the method was found to have the requisite features of specificity and sensitivity for monitoring plasma levels of selected tea polyphenols.

Chromatography, High Pressure Liquid↗
PubMed1988

[Effects of the treatment of coffee pulp, fresh or ensilaged, with calcium hydroxide, on its nutritive value].

This study was carried out to determine the effects of the addition of calcium hydroxide on the chemical composition and nutritive value of fresh or ensilaged coffee pulp. Fresh or ensilaged pulp were mixed with 1, 2 and 3% of calcium hydroxide. The process was carried out during 0 and 16 hr, after which time the treated pulp was sun-dried for 36 hr until moisture content reached 12%. These samples were then analyzed for their proximate chemical composition and for some minerals (Ca, P, Na, K), as well as for caffeine, tannins and chlorogenic and caffeic acids content. Diets were then prepared from these materials, containing 15% protein and 15 or 30% fresh or ensilaged coffee pulp, and offered to weanling rats during six weeks. Information required on weight gain, food conversion, apparent digestibility and toxicity of the diets was recorded. Results of the chemical analysis revealed that the main changes found in both types of pulp as a result of the calcium hydroxide treatment were the following: a decrease in ether extract (from 4.0 to 2.5 g/100 g), crude fiber (from 18.3 to 11.9 g/100 g) and protein content (from 12.3 to 8.6 g/100 g) in an inverse relation to the amount of calcium hydroxide used. The amount of ash increased, fluctuated between 5.5 and 15.4%, depending on the amount of calcium hydroxide used. The latter affected the Ca:P ratio in the diets, where an average ratio of 7.2:1 was found in the control pulp (0% calcium hydroxide) and 59.0:1 in those treated with the highest amount of calcium hydroxide (3%). Regarding the caffeine, tannins and chlorogenic and caffeic acids contents, calcium hydroxide was effective in decreasing only tannins, more so in the fresh than in the ensilaged pulp; the decrease was in direct proportion to the amount of calcium hydroxide added and to the length of the Ca(OH)2 treatment. The results of the biological assays showed that the addition of Ca(OH)2 in either of the two time periods used and at either of the concentrations studied, did not improve the nutritive value of coffee pulp. There was always a better performance in the animals that consumed ensilaged pulp than in those fed fresh pulp. The animals fed 15% coffee pulp either fresh or ensilaged performed better than those consuming 30% coffee pulp.(ABSTRACT TRUNCATED AT 400 WORDS)

Animals↗
PubMed2006

Antitumor activity of some natural flavonoids and synthetic derivatives on various human and murine cancer cell lines.

The effect of various natural flavonoids, cinnamic acid derivatives, and a series of synthetic flavones on cell proliferation was evaluated in vitro in a panel of established human and murine tumor cell lines. The most potent antiproliferative agents were caffeic acid n-butyl ester (12) > 2'-nitroflavone (26) > caffeic acid ethyl ester (11) approximately = 2',6-dinitroflavone (27) > apigenin (3) > 3'-bromoflavone (20) approximately = 2'-fluoro-6-bromoflavone (31). Some compounds showed a moderate effect, the order of cytotoxic activities being chrysin (2) > 2'-fluoro-6-chloroflavone (30) approximately = 2'-chlorochrysin (32) > alpha-naphthoflavone (7) > beta-naphthoflavone (8) approximately = 6-chloroflavone (14) approximately = 6-bromoflavone (15) approximately = 4'-nitroflavone (23). A structure-activity relationship analysis of each group of compounds was performed. None of the natural or synthetic compounds tested affected the proliferation of epithelial cells derived from normal mammary gland of mice or fibroblastic cells from mouse embryo, suggesting a selective action against tumor cells.

Animals↗
PubMed1998

Synthesis and anti-human immunodeficiency virus type 1 integrase activity of hydroxybenzoic and hydroxycinnamic acid flavon-3-yl esters.

A series of new hydroxybenzoic and hydroxycinnamic acid flavon-3-yl esters were synthesized in order to obtain compounds targeting the human immunodeficiency virus (HIV) type 1 integrase (IN). The esters were tested for anti-IN and anti-reverse transcriptase (RT) activity in enzyme assays and for anti-HIV-1, anti-proliferative and anti-topoisomerase activity in cell-based assays. In enzyme assays, the two gallic acid flavon-3-yl esters showed a notable IN inhibition (IC50 values were 8.3 and 9.1 microM, respectively), while the two caffeic acid flavon-3-yl esters exhibited a modest activity (IC50 75 and 60 microM, respectively). Replacement of hydroxyl groups resulted in loss of potency. Caffeic acid 3',4'-dichloroflavon-3-yl ester also inhibited the RT activity whereas it was not active on human topoisomerases. It therefore represents an interesting example of a compound specifically targeting more than one step of the virus replication cycle.

Anti-HIV Agents↗
PubMed1992

Structure and expression of the lignin O-methyltransferase gene from Zea mays L.

The isolation and characterization of cDNA and homologous genomic clones encoding the lignin O-methyltransferase (OMT) from maize is reported. The cDNA clone has been isolated by differential screening of maize root cDNA library. Southern analysis indicates that a single gene codes for this protein. The genomic sequence contains a single 916 bp intron. The deduced protein sequence from DNA shares significant homology with the recently reported lignin-bispecific caffeic acid/5-hydroxyferulic OMTs from alfalfa and aspen. It also shares homology with OMTs from bovine pineal glands and a purple non-sulfur photosynthetic bacterium. The mRNA of this gene is present at different levels in distinct organs of the plant with the highest accumulation detected in the elongation zone of roots. Bacterial extracts from clones containing the maize OMT cDNA show an activity in methylation of caffeic acid to ferulic acid comparable to that existing in the plant extracts. These results indicate that the described gene encodes the caffeic acid 3-O-methyltransferase (COMT) involved in the lignin bio-synthesis of maize.

Amino Acid Sequence↗
PubMed1992

Solid-phase extraction and HPLC determination of 4-vinyl guaiacol and its precursor, ferulic acid, in orange juice.

This study is undertaken to develop a simplified, rapid method to determine both immediate and potential off odors due to 4-vinyl guaiacol and its odorless precursor, ferulic acid, from a single sample preparation and chromatographic analysis. Orange juice sample preparation consists of a simple, C18 solid phase extraction. Utilizing a 5-microns, 25-cm, C18 column, both compounds can be separated within 40 min using a one-step, linear gradient beginning with an aqueous 12% tetrahydrofuran (THF)-5% acetonitrile mixture and ending with 35% aqueous THF. Hesperidin and nariutin have been identified as the compounds that interfered with the ultraviolet (UV) determination of sinapic and caffeic acids. Fluorescence detection with wavelength programming offers optimal sensitivity and selectivity. Recoveries of 4-vinyl guaiacol and ferulic acid range from 90 to 103%. Detection limits are 1 ppm and 5 ppm for ferulic acid and 4-vinyl guaiacol, respectively. Other hydroxycinnamic acids such as coumaric, sinapic, and caffeic acids may also be determined from the same chromatogram.

Beverages↗
PubMed1993

Acylated flavonol glycosides from cabbage leaves.

Seven flavonol glycosides were isolated from a leaf extract of cabbage and characterized by chemical and spectroscopic methods including 1H and 13C NMR and negative ion FAB-MS. Five compounds were new natural products or were fully characterized for the first time. They are derivatives of kaempferol-3-O-beta-D-sophoroside-7-O-beta-D-glucoside acylated at C-2"' with either caffeic acid, p-coumaric acid or ferulic acid, and of quercetin-3-O-beta-D-sophoroside-7-O-beta-D-glucoside acylated with either caffeic acid or ferulic acid. Kaempferol-3-O-beta-D- sophoroside-7-O-beta-D-glucoside and kaempferol-3-O-beta-D-(2-sinapoylsophoroside)-7-O-beta-D-glucoside were found for the first time in cabbage, but they have previously been found in other Brassica species.

Brassica↗
PubMed2002

Monolignol biosynthesis in microsomal preparations from lignifying stems of alfalfa (Medicago sativa L.).

Microsomal preparations from lignifying stems of alfalfa (Medicago sativa L.) contained coniferaldehyde 5-hydroxylase activity and immunodetectable caffeic acid 3-O-methyltransferase (COMT), and catalyzed the S-adenosyl L-methionine (SAM) dependent methylation of caffeic acid, caffeyl aldehyde and caffeyl alcohol. When supplied with NADPH and SAM, the microsomes converted caffeyl aldehyde to coniferaldehyde, 5-hydroxyconiferaldehyde, and traces of sinapaldehyde. Coniferaldehyde was a better precursor of sinapaldehyde than was 5-hydroxyconiferaldehyde. The alfalfa microsomes could not metabolize 4-coumaric acid, 4-coumaraldehyde, 4-coumaroyl CoA, or ferulic acid. No metabolism of monolignol precursors was observed in microsomal preparations from transgenic alfalfa down-regulated in COMT expression. In most microsomal preparations, the level of the metabolic conversions was independent of added recombinant COMT. Taken together, the data provide only limited support for the concept of metabolic channeling in the biosynthesis of S monolignols via coniferaldehyde.

Chromatography, High Pressure Liquid↗